ursolic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ursolic acid
• 英文别名: 3-epiursolic acid；3α-hydroxyurs-12-en-28-oic acid；3-epi-Ursolsaeure；3-epi-Ursonic acid；TP-52；(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: WCGUUGGRBIKTOS-XHINXETDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ursolic acid 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.83h， 生成 3α-O-(β-D-glucopyranosyl)-urs-12-en-28-oic acid benzyl ester
  参考文献：
  名称：

  Structure-aided optimization of 3-O-β-chacotriosyl epiursolic acid derivatives as novel H5N1 virus entry inhibitors

  摘要：

  It is urgent to develop new antiviral agents due to the continuous emergence of drug-resistant strains of influenza virus. Our earlier studies have identified that certain pentacyclic triterpene saponins with 3-O-β-chacotriosyl residue are novel H5N1 virus entry inhibitors. In the present study, a series of C-28 modified 3-O-β-chacotriosyl epiursolic acid derivatives via conjugation with different kinds of sides were synthesized, of which anti-H5N1 activities in A549 cells were evaluated in vitro. Among them, 10 exhibited strongest anti-H5N1 potency at the low-micromole level without cytotoxicity, surpassing the potency of ribavirin. Further mechanism studies of the lead compound 10 based on HI, SPR and molecular modeling revealed that these new 3-epiursolic acid saponins could bind tightly to the viral envelope HA protein, thus blocking the invasion of H5N1 viruses into host cells.

  DOI：

  10.1016/j.bmcl.2020.127518
• 作为产物：
  描述：

  熊果酸 在 potassium carbonate 、 氯化苄 、 戴斯-马丁氧化剂 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 12.0h， 以67.6%的产率得到ursolic acid
  参考文献：
  名称：

  Betulinic acid作为PS1 / BACE1相互作用减少Aβ生成的强抑制剂的合成类似物

  摘要：

  紫杉烷型三萜具有多种生物活性，例如抗病毒，抗炎和抗癌活性。我们在这里描述其作为PS1 / BACE1相互作用抑制剂在阿尔茨海默氏病（AD）治疗中的潜在应用。发现高通量筛选（HTS）产生的3- α-链烷酸会干扰PS1 / BACE1相互作用并减少淀粉样β-蛋白（Aβ）的产生。鉴于来源有限，我们改用天然富硒的桦木酸（化合物2）作为铅优化的起始原料，并构建了其衍生物的聚焦库，以更好地了解三萜类化合物的结构活性关系（SAR） PS1 / BACE1相互作用的抑制剂。化合物22 最终被选为最有效的PS1 / BACE1相互作用抑制剂，可有效减少Aβ的产生。

  DOI：

  10.1002/cjoc.201600611

文献信息

• Naturally Occurring Pentacyclic Triterpenes as Inhibitors of Glycogen Phosphorylase: Synthesis, Structure−Activity Relationships, and X-ray Crystallographic Studies
  作者：Xiaoan Wen、Hongbin Sun、Jun Liu、Keguang Cheng、Pu Zhang、Liying Zhang、Jia Hao、Luyong Zhang、Peizhou Ni、Spyros E. Zographos、Demetres D. Leonidas、Kyra-Melinda Alexacou、Thanasis Gimisis、Joseph M. Hayes、Nikos G. Oikonomakos

  DOI：10.1021/jm8000949

  日期：2008.6.1

  Twenty-five naturally occurring pentacyclic triterpenes, 15 of which were synthesized in this study, were biologically evaluated as inhibitors of rabbit muscle glycogen phosphorylase a (GPa). From SAR studies, the presence of a sugar moiety in triterpene saponins resulted in a markedly decreased activity ( 7, 18- 20) or no activity ( 21, 22). These saponins, however, might find their value as potential

  二十五个天然存在的五环三萜，在本研究中合成了十五个，被生物评估为兔肌肉糖原磷酸化酶α（GPa）的抑制剂。根据SAR研究，三萜皂苷中糖部分的存在导致活性显着降低（7、18-20）或无活性（21、22）。但是，这些皂苷可能具有潜在的天然前药价值，它们的水溶性比其相应的糖苷配基要高得多。为了阐明GP抑制的机制，我们确定了GPb-亚硫酸和GPb-山梨酸复合物的晶体结构。X射线分析表明，抑制剂在生理活化剂AMP结合的变构活化剂位点结合。
• Studies on the constituents of medicinal and related plants in sri lanka. I. New triterpenes from Hedyotis lawsoniae.
  作者：TOHRU KIKUCHI、SATOKO MATSUDA、SHIGETOSHI KADOTA、YOSHIKO SAKAI、TSUNEO NAMBA、KAZUO WATANABE、RAN BANDA DISSANAYAKE DISSANAYAKE MUDIYANSELAGE

  DOI：10.1248/cpb.32.3906

  日期：——

  Three new triterpene acids were isolated from the twigs and leaves of Hedyotis lawsoniae, together with sixteen known ones. The new compounds were determined to be 3β, 23-dihydroxyurs-12-en-28-oic acid, 3β, 24-dihydroxyurs-12-en-28-oic acid, and 2α, 3β, 24-trihydroxyurs-12-en-28-oic acid on the basis of spectroscopic evidence.

  从 Hedyotis lawsoniae 的树枝和树叶中分离出了三种新的三萜酸以及十六种已知的三萜酸。根据光谱证据，新化合物被确定为 3β、23-二羟基乌苏-12-烯-28-酸、3β、24-二羟基乌苏-12-烯-28-酸和 2α、3β、24-三羟基乌苏-12-烯-28-酸。
• Hair composition
  申请人：Conopco, Inc.

  公开号：US10456344B2

  公开（公告）日：2019-10-29

  Disclosed is an oral or topical composition comprising a nuclear factor erythroid-2 related factor 2 agonist and a liver X receptor agonist, wherein the amounts of each of the nuclear factor erythroid-2 related factor 2 agonist and the liver X receptor agonist produce a synergistic benefit of hair fiber growth, wherein the oral or topical composition comprises ≤9, preferably ≤8% w/w β-sitosterol, wherein when the oral or topical composition comprises a catechin, the oral or topical composition comprises 0.001 to 90, preferably 0.005 to 70, most preferably 0.01 to 50% w/w catechins, wherein the oral or topical composition excludes pregnenolone, 4, 5-dihydrofuranodiene-6-one, epoxy santamarin, hydroquinone, longistyline, monacolin K, protoanemonin, N-(2,2,2-tri-fluoro-ethyl)-N-[4-(2,2,2-tri-fluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-benzenesulfonamide, dihydronepetalactone, iridomyrmecin, and dihydroactinidiolide, wherein when the oral or topical composition comprises guggelsterone and epigallocatechin gallate, the oral or topical composition excludes a guggelsterone to epigallocatechin gallate weight ratio of 1 to 28, and wherein when the oral or topical composition comprises sodium dilauramide glutamide lysine, the oral or topical composition excludes 0.3% w/w sodium dilauramide glutamide lysine.

  公开了一种口服或外用组合物，该组合物包含核因子红细胞生成素-2 相关因子 2 激动剂和肝 X 受体激动剂，其中核因子红细胞生成素-2 相关因子 2 激动剂和肝 X 受体激动剂各自的用量对毛发纤维生长产生协同益处，其中口服或外用组合物包含 ≤9% w/w，优选 ≤8% w/w β-谷甾醇，其中当口服或外用组合物包含儿茶素时，口服或外用组合物包含 0.001至90，优选0.005至70，最优选0.其中口服或外用组合物不包括孕烯醇酮、4, 5-二氢呋喃二烯-6-酮、环氧山奈酚、对苯二酚、龙胆紫、莫那可林 K、原橙皮甙、N-(2,2,2-三氟-乙基)-N-[4-(2,2,2-三氟-1-羟基-1-三氟甲基乙基)-苯基]-苯磺酰胺、二氢吡咯内酯、鸢尾霉素和二氢吡咯内酯、其中，当口服或外用组合物包含钩藤甾酮和表没食子儿茶素没食子酸酯时，口服或外用组合物排除钩藤甾酮与表没食子儿茶素没食子酸酯的重量比为1比28，并且其中，当口服或外用组合物包含二月桂酰胺谷酰胺赖氨酸钠时，口服或外用组合物排除0.3% w/w 的二月桂酰胺谷酰胺赖氨酸钠。
• HAIR COMPOSITION
  申请人：Conopco, Inc., d/b/a UNILEVER

  公开号：US20170360673A1

  公开（公告）日：2017-12-21

  Disclosed is an oral or topical composition comprising a nuclear factor erythroid-2 related factor 2 agonist and a liver X receptor agonist, wherein the amounts of each of the nuclear factor erythroid-2 related factor 2 agonist and the liver X receptor agonist produce a synergistic benefit of hair fibre growth, wherein the oral or topical composition comprises ≦9, preferably ≦8% w/w β-sitosterol, wherein when the oral or topical composition comprises a catechin, the oral or topical composition comprises 0.001 to 90, preferably 0.005 to 70, most preferably 0.01 to 50% w/w catechins, wherein the oral or topical composition excludes pregnenolone, 4, 5-dihydrofuranodiene-6-one, epoxy santamarin, hydroquinone, longistyline, monacolin K, protoanemonin, N-(2,2,2-tri-fluoro-ethyl)-N-[4-(2,2,2-tri-fluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-benzenesulfonamide, dihydronepetalactone, iridomyrmecin, and dihydroactinidiolide, wherein when the oral or topical composition comprises guggelsterone and epigallocatechin gallate, the oral or topical composition excludes a guggelsterone to epigallocatechin gallate weight ratio of 1 to 28, and wherein when the oral or topical composition comprises sodium dilauramide glutamide lysine, the oral or topical composition excludes 0.3% w/w sodium dilauramide glutamide lysine.
• [EN] SYSTEMS AND METHODS FOR COMBINED COSMETIC TREATMENT OF CELLULITE WITH ULTRASOUND<br/>[FR] SYSTÈMES ET PROCÉDÉS DE TRAITEMENT COSMÉTIQUE COMBINÉ DE LA CELLULITE PAR ULTRASONS
  申请人：ULTHERA INC

  公开号：WO2019164836A1

  公开（公告）日：2019-08-29

  Dermatological cosmetic combination treatments with high intensity focused ultrasound, dermal fillers, fat-reducing compounds, cavitation-prone fluids, and/or septa dissection are provided. A HIFU therapy system can include an imaging system, methods adapted to alter placement and position of a line focus band therapy, multiple simultaneous cosmetic ultrasound treatment zones in tissue, and dithering ultrasound beams from a transducer to alter placement and position of multiple cosmetic treatment zones in tissue. The HIFU systems can include a hand wand, removable transducer modules, and a control module. The dermal fillers can include hydroxyapatite. The fat-reducing compounds can include adipocytolytic compounds, pentacyclic triterpenoid compounds, proapoptotic compounds, compounds impairing differentiation of pre-adipocytes, and combinations thereof. The cavitation-prone fluids can include molecules dissolved in fluids, ethanol, glycerin, and ethylene glycol. The septa dissecting can include using a cutting blade and/or cavitation HIFU. The cosmetic treatment system may be used in various cosmetic procedures, such as treating cellulite.